Before I say anything about D-Hall, let me make it clear that I don't think he's a top corner or anything. But he does have a knack for taking away a team's top receiver. For example, Dez Bryant constantly struggles against him. In addition to that, London Fletcher has retired so experience is already running thin on the defensive side of the ball. I would think that Gruden will take a CB in the 4th or 5th round and maybe another in the 6th or 7th. You do want guys like Deangelo who are experienced and provide some sort of reliability. So, I'm not exactly thrilled to have him back on the team but I completely understand why Gruden would want to keep him around.
Having D-Hall on the team isn't a problem in my book, what I'm concerned about is who we are going to draft.
As far as Gruden's days at Cincy are concerned, I think that has more to do with Marvin Lewis and Andy Dalton. Dalton can't make clutch throws when the game is on the line and he is absolutely awful on 3rd down. Being terrible on 3rd down will kill you in the playoffs. Here is an interesting article showing how QB's perform on 3rd and 4th down. Now the article is from 2013, but I still think it's relevant in this case.
https://www.profootballfocus.com/blog/2 ... rterbacks/
You'll notice that Dalton is next to last on this list. He''s only ahead of Chad Henne. You could argue that Dalton has one of the best surrounding cast in the league, so, there really is no excuse for being that bad. I don't blame one bit of that on Gruden.